Serena Williams: The Champion’s Mindset

In the first in-depth interview about her new, self-funded brand, the world-class tennis player talks to BoF about her love of fashion, her previous challenges in the space and how on-court successes and setbacks have helped prepare her for entrepreneurship.

Serena Williams: The Champion’s Mindset

In the first in-depth interview about her new, self-funded brand, the world-class tennis player talks to BoF about her love of fashion, her previous challenges in the space and how on-court successes and setbacks have helped prepare her for entrepreneurship.

Discover the essential tools for successful entrepreneurship in BoF’s Start-Up School: a resource comprised of a practical guide on topics ranging from fundraising and finding product-market fit to planning an exit; along with supplemental tools, templates and frameworks. Become a member to access.

LOS ANGELES, United States — Serena Williams has just come back from tennis practice and collapses into a chair at her home in Beverly Hills. The only visible hints of her status as a tennis legend are the gold, racket-shaped earrings dangling discreetly from her ears.

The hubbub at her house is not unlike family scenes unfolding at homes across America — except Williams is no ordinary working mom. For one, she gave birth to her daughter, Alexis Olympia Ohanian Jr, (named after husband and Reddit founder Alexis Ohanian), in September 2017, just seven months after winning her 23rd Grand Slam title at the Australian Open. Soon after she gave birth, blood clots travelled to her lungs, leading to a pulmonary embolism and several other serious post-labour complications that threatened to take her life. But even this hasn’t slowed her down.

It’s been a packed week for Williams. Just a few days earlier she was co-hosting a lavish baby shower for her friend Meghan Markle (now the Duchess of Sussex, following her marriage to Prince Harry, sixth in the line of succession to the British throne) at the Mark Hotel in New York. “Planning something like that takes a lot of effort. I’m a perfectionist, so I’m like, ‘Let’s make it perfect,’” she explains. “It’s been a lot the last few days.”

Today, Williams is gearing up for yet another star turn, this time at the 91st Academy Awards where she is set to introduce best picture nominee “A Star is Born,” featuring Bradley Cooper and Lady Gaga.

But that’s not all. On top of the tennis, the baby and her A-list social calendar, Serena Williams recently became the founder and chief executive of her own direct-to-consumer brand, S by Serena, her latest attempt to crack the fashion business.

“I always joke with my husband that I never thought I would have my own start-up, but I have my own start-up now and it’s going pretty well!” she says enthusiastically. “It hasn’t even been a year. We launched 10 months ago officially, even though we’ve been working on it for two and a half, three years — and in my mind since I was a teenager.”

I didn’t want to have the exact same look that everyone else was wearing. I like to stand out.

Indeed, Williams’ longstanding interest in fashion will come as no surprise to her fans, who have followed her meteoric rise since she and her sister Venus first arrived on the tennis scene in the 1990s, with their exceptional physiques, unstoppable serves and bold on-court outfits.

But why try her hand at launching a fashion line again, and why now?

Fashion On and Off the Court

“I’ve always loved fashion,” she says. “I remember when I was a kid, my mom used to make all our outfits. Back then, they had Vogue patterns. I would always see her pinning them and making all our clothes. And she taught us how to sew early on. So, I used to sew clothes for my dolls out of old socks and I would cut them up and make little outfits out of them,” she laughs.

“Eventually after high school — somewhere in between winning Wimbledon and several US Opens — I went to art school,” she continues. Williams studied fashion at the Art Institute of Fort Lauderdale in Florida from 2000 to 2003. “I excelled at pattern making. I think it’s because I love mathematics and I like the technical part.”

But eventually, her professional tennis career took priority. By July 2002, she was ranked the world’s number-one singles player by the Women’s Tennis Association for the first time. She would later hold the number one rank on eight separate occasions for a total of 319 weeks between 2002 and 2017, winning 23 Grand Slam singles titles, 14 Grand Slam women’s doubles titles, and two Grand Slams in mixed doubles, as well as four Olympic gold medals, one in women’s singles and three in women’s doubles.

Occasionally, her fashion training came in handy on the tennis tour. “I remember one time playing a tournament and, after I won, I put on a skirt to take a picture and my skirt broke,” she laughs. “Everyone in the locker room was like, ‘Oh, the seamstress left.’ And I’m like, ‘Well, did she leave her stuff?’ And they were like, ‘Yeah,’ so I said, ‘I’ll get it.’

“Yeah, it was just a simple stitch, you know, I could have hand-sewn it too,” she says gamely. “And everyone’s jaws were on the floor!”

Throughout her tennis career, Williams has been a careful curator of her personal brand, often using fashion statements to craft her public image. On the court, she has worn tutus, catsuits, denim miniskirts and even statement jewellery. “This is where a lot of people see me and I’m a super creative,” she says. “It’s like, how do I express who I am? That’s one thing I love about clothes. You can express how you’re feeling [and] who you are by what you wear. I didn’t want to have the exact same look that everyone else was wearing. I like to stand out.”

Over the years, Williams went from customising her own outfits to working with sponsor Nike to create show-stopping looks. Most recently, she worked with Virgil Abloh to create the “Queen” collection she wore at the US Open last August. “In the beginning I really was able to push the envelope and now we work with great designers that really get it, and they push it with me.”

Sometimes her sartorial choices have created controversy, most recently at the French Open in 2018. It was Williams’ first grand slam tournament since the birth of her daughter. For her triumphant return, she wore a black one-piece Nike catsuit with a single red stripe, designed to help prevent further blood clots. Afterwards, she said it made her feel like a “superhero,” telling USA Today that it represented “all the moms out there that had a tough pregnancy and have to come back and try to be fierce, in [the] middle of everything.”

It’s so easy when you’re so successful at something else to just do that... But that’s not the story I wanted to tell.

But the French Tennis Federation wasn’t having it. The association’s president, Bernard Giudicelli, said that they would “impose certain limits” on clothing that can be worn during the event, beginning with the 2019 French Open. “It will no longer be accepted. One must respect the game and the place,” he said, sparking a global debate. Former tennis champion, Billie Jean King, tweeted support for Williams: “The policing of women’s bodies must end. The ‘respect’ that’s needed is for the exceptional talent @serenawilliams brings to the game. Criticising what she wears to work is where the true disrespect lies.”

Williams’ first real fashion venture was a brand called Aneres, Serena spelled backwards, And, like many entrepreneurs, her journey started with a failure.

“Everyone that goes to fashion school wants to do eveningwear,” Williams reflects. “I stuck with that for years and years and I loved it. But I was doing evening gowns and we never actually sold anything — nothing that people could really actually buy in store. We did some amazing shows and I was able to be super creative in those shows, from head-to-toe, from makeup to eyelashes to shoes to nail polish. Literally every decision was based on what I wanted… But it didn’t work,” she sighs. “So many times, I would be at a meeting with Macy’s or lots of other companies and they would be like, ‘We love it. We love the presentation, but we’re not going to get this collection.’ I’ve sat through so many of those meetings, more than I can count to be honest. And they’re demoralising.”

“Eventually I got realistic. I can’t do eveningwear, so let me think of different things that I can do,” Williams recounts. “And that’s when I got into just sportswear stuff, more everyday wear. And then I ended up attaching myself with HSN, which was really good.”

The Home Shopping Network partnership, under the brand name Serena Signature Statement, began in 2014 with see-now-buy-now shows staged at New York Fashion Week. But Williams wasn’t satisfied and after three shows the partnership ended. “I learned a lot, but I felt like there was so much more I wanted to do at a different demo, a broader demo that I wanted to reach. Design-wise, there was only so many fabrics you could use. It just wasn’t me. As much as we pushed for a label at HSN, it still wasn’t what I wanted to do,” she recalls.

“And then one day I was talking to my friend, and she was like, ‘Oh, you know, I really love my music and I don’t want to give up.’ And I was like, well, sometimes you have to invest in yourself and if people don’t want to invest in you, you have to believe in yourself and invest in yourself,” she recounts. “And then I stopped. It hit me like a ton of bricks. I was like, ‘Oh my God, all this time I have been doing different things and meeting different people and doing HSN, but I’d never actually invested in me.’ So, I was like, ‘I’m investing in me!’”

With more than $86 million in career prize money, and millions more in endorsements from Nike, Audemars Piguet and Beats, among others, Williams is the highest-earning female athlete of all time and is certainly in a financial position to fund her own business. She is also an investor in many other start-ups founded by women and minorities, but until recently she never considered backing her own ambitions in fashion entrepreneurship.

“I’ve been trying for years and years to do something in fashion. I’ve been doing this for so long and it’s never hit,” she confesses. “It’s so easy when you’re so successful at something else to just do that and keep being amazingly successful at it. But that’s not the story I wanted to tell. And I always felt like if I didn’t at least do it one more time, a 100 percent with my backing, that I would always have some sort of regret.”

Surprisingly, there is nothing at all sporty or athletic about Serena’s new collection. Due to her Nike contract, there are constraints on what Williams can sell through her own line. “I can’t do athletic wear or athleisure,” she explains, nonplussed. But whereas many would see this as a stumbling block for a world-famous athlete launching a line, she sees it as an opportunity. “Right now, I think the market might be really saturated with athleisure.”

Instead, Williams’ first collection under her latest brand is squarely focused on accessibly priced fashion basics with a colourful punch. It’s also an inclusive line, available in a wide range of sizes for women with varying body types.

While Williams declined to disclose business performance, her new line has certainly caught on with one famous customer. Last October, her friend Meghan Markle was seen wearing the “boss blazer” during the royal tour of Australia, which the company says has become a best-seller for the brand.

I’ve been trying for years and years to do something in fashion. I’ve been doing this for so long and it’s never hit.

“It’s so fun because people are like, ‘Oh my God. Like wow, the quality is crazy,’” she says proudly. “Listen, if we’re giving our stuff to Meghan, it has to be the highest quality that we can get. So, that’s what I tell our team internally: ‘We have to make sure it’s super high quality that, you know, is fit for a royal princess!’”

When big PR moments like this happen, Williams is more than happy to seize the opportunity, though all of her products are created as limited-edition drops only. “We don’t really like to re-order,” she explains. “We turn around a lot of stuff really fast — but we don’t have a ton of inventory. We don’t have 5,000 units. We have a lower number of units and then we just keep turning it around. Fast fashion seems to be every week — we do it, like, twice a month or maybe once a month.”

Alongside the “boss blazer,” other key items include T-shirts and sweatshirts emblazoned with positive slogans like “I am strong, I am beautiful.” The vast majority of her SKUs are under $200. But not everything is basic. “Sometimes there’s pieces in there that are a little less wearable — but very few. Those are what we call our marketable pieces that get a lot of attention. You have to really look at our website and almost be a fan to understand some of the lingo, like the GOAT collection (“greatest of all time”) is exclusive pieces.”

For now, Williams controls her distribution, keeping the business strictly direct-to-consumer, via her e-commerce website and occasional pop-up events scheduled around global events, including the US Open and Art Basel Miami.

“As someone who appreciates fashion and follows the industry, Serena is well aware of the rapidly changing retail market,” says longtime supporter Anna Wintour, the artistic director of Condé Nast and editor of American Vogue, who has put Williams on the cover of her magazine three times. “Like many entrepreneurs of her generation, she has decided to forego traditional retail stores, a move that makes sense given the level of connection with her audience.”

If you truly love what you do then setbacks are just a motivation for you to keep going.

Williams’ audience is most certainly vast. With more than 10 million fans on Instagram and a personal brand more than 20 years in the making, there is no doubt about the commercial potential of a brand linked to the star power of the world-class athlete. Thus far, the S by Serena fashion line has attracted 169,000 followers on Instagram. Yet, how this translates into fashion and other categories remains to be seen.

What’s more, direct-to-consumer sales usually lead to favourable margins. But Williams is still figuring out the unit economics and trying to strike the right balance between price and quality. “Our margins are sometimes a little bit lower than I would like to see,” she admits. “I just tell the team it’s going to pay off in the end, because eventually people will be able to see the high quality that we have and be like, ‘wow this is great.’”

“You know, in the beginning it never pays off,” she adds. “I was reading a book about Amazon and — believe me, I am not comparing myself to Jeff Bezos in any way, shape or form — but they were down a billion before they made their first dollar and that was so encouraging to me. I was like, ‘Okay, we’re doing so much better than that.’ We just started in May and we have all this stuff coming, and eventually we’re coming out with beauty and then we have jewellery,” she says.

Mental Toughness from the Court

The start-up journey has not been easy for Serena Williams. But her on-court success has been a support in more ways than one.
“Everything that I’ve been doing in my life and tennis, I can relate everything to entrepreneurship,” Williams says. “Everyone can win when people are supporting them or giving them money and backing their careers. Of course they’re going to win. But if something happens and you fall, how do you recover? How do you come back? How do you change the narrative? How do you be true to yourself and be authentic? For me, it’s the same for the greatest entrepreneurs.”

“Everything that Serena takes on, she approaches fearlessly and wholeheartedly,” says Wintour. “The same unwavering dedication that makes her a champion on the court carries over into every aspect of her life — whether that be in business, motherhood or tennis. Serena decisively commits to any endeavour that she pursues.”

Williams is one of those rare athletes who has transcended her sport to become something bigger. As a black woman who rose out of the Compton ghetto and won her first Grand Slam tennis championship at the age of 17, becoming the number-one player in the world in a sport dominated by white athletes, Williams is a powerful symbol of the American Dream and a hero for millions of people around the world.

“She’s always been about empowerment,” says Jill Smoller, a partner at William Morris Endeavour who has been Williams’ manager for more than 20 years. “A lot of the topics that are on the forefront of the conversation in the media and society right now — such as racism, sexism — are all things Serena has been speaking out against her whole career, and it is what has made her now one of the most influential people in the world. The things that used to hold her back are now propelling her, and helping her create effective change in the world.”

These experiences have undoubtedly made her stronger. “When I first started, I had to work so hard to get to where I am. Whenever I step on that court, I work really hard. And even in fashion, hearing the word ‘No’ I don’t know how many times. That made me want to work hard because I’ve heard the word ‘No’ in tennis before, too. That just brings me back to those memories. If it wasn’t for those setbacks, we wouldn’t be where we are with the business right now.”

Speaking of setbacks, last September at the US Open finals, Williams was on the cusp of winning her 24th Grand Slam, which would have put her in a tie with Margaret Court as the tennis player — male or female — with the highest number of Grand Slam titles. But in the final match against rising star Naomi Osaka, Williams’ coach Patrick Mouratoglou was observed making hand gestures that umpire Carlos Ramos interpreted as coaching, which is strictly forbidden on the professional tour.

Williams denied this, saying she would “never cheat to win and would rather lose“ and soon this escalated into a shouting match with Ramos. Later, Osaka was awarded a point after Williams smashed her racquet, something that countless male tennis players have done over the years without penalty. A debate erupted on social media and in newspapers around the world, with some suggesting that Williams’ career-long fight against double standards, racism and sexism was far from over.

Why do I have to face a different standard than the man?

I ask if she regrets losing her cool that day. “That’s a really loaded question,” she says. “Do I feel regret for being penalised for something which has never happened in the history of tennis and I didn’t use one single curse word? And what, do I feel regret over that?”

I explain that there are days when all of us wish we might have handled a given situation differently. It’s about the process of learning to be our best selves in the midst of the intense emotions that can come with professional ambition, whether that be building your own business or being a professional athlete.

She pauses and reflects: “For me, being a perfectionist and being a professional, it would be impossible not to wish I didn’t handle a lot of situations differently, even that particular situation. So, absolutely. However, I have to tell myself, because of my daughter, that I should be able to have any emotion that any man can have. It’s about teaching our new generation that everyone should be treated the same.”

Williams, who sits on the board of Survey Monkey, recalls the data from a recent survey of women, which asked about managing emotions in the workplace. “A lot of women said they feel they have to manage their emotions because they’re called ‘too emotional’ or they’re called something else just because we face different challenges than men face. So, I always think about that. Why do I have to face a different standard than the man?”

Over the years, Williams has also shown a remarkable resilience and tenacity through constant public scrutiny. “It’s part of life, you know,” she says matter-of-factly. “If someone’s not scrutinising you or talking about you, then you’re not doing something right. If everyone’s praising you and everything’s perfect, then it’s not the real world. People are going to scrutinise you no matter what. They’ll find something wrong with you even if you’re not doing anything wrong. And I don’t let that affect me anymore. I think in the past I did,” she admits.

According to a study undertaken by researchers at the University of California, San Francisco, entrepreneurs are 50 percent more likely to report mental health conditions. They are two times more likely to suffer from depression, six times more likely to suffer from ADHD and 10 times more likely to suffer from bipolar disorder. So how does Williams advise entrepreneurs to keep bouncing back, as she has consistently done in her tennis career?

Serena Williams | Photo: Allyssa Hueze

“I can really only do so as it relates to tennis because my fashion brand isn’t a billion-dollar business — yet,” she says. “There have been so many times I was like, ‘I should just stop. This is pointless. I don’t have to do this.’ But I love what I do. And if you truly love what you do then setbacks are just a motivation for you to keep going. You get through it by knowing that it’s vital to have setbacks, or you won’t appreciate it when you make it.”

Williams is on a tight schedule and we’re almost out of time. Before she leaves for her Oscars rehearsal, I ask about visualisation, another technique she is known to use to achieve her tennis goals, even writing herself little match notes like “You’re number one” and “Play with a purpose!”

“Millions of people have ideas every day and they just remain ideas. But how do you get the idea to become something successful? I am a strong believer in visualisation. It’s like this meditation. You need to see things happening and envision yourself in a fantasy world, and really believe in that fantasy world until it comes true — or else it’s just going to be an idea.”

So how does she visualise her business going forward?

“I’m not going to tell you,” she replies instantly.

“Why not?” I ask.

“I don’t want to jinx myself, but it’s definitely way bigger than what we’re talking about. I have huge plans for this brand. Whenever I have a goal, even in tennis, I just keep it to myself and among my tennis team. For fashion, I keep it with our business team and we just have it on a board and work towards it every day.”

Lessons in Mental Toughness

On Failure

“You’ve got to have really thick skin and not take anything personally, even though it might be hard to hear. It’s the same in sport. You have to have super thick skin, especially me. And you can’t take anything too personally because you have to be back in the next week, in our sport, to play again.”

On Visualisation

“Millions of people have ideas every day and they just remain ideas. But how do you get the idea to become something successful? I am a strong believer in visualisation. It’s like this meditation. You need to see things happening and envision yourself in a fantasy world, and really believe in that fantasy world until it comes true — or else it’s just going to be an idea.”

On Resilience

“There have been so many times I was like, ‘I should just stop. This is pointless. I don’t have to do this.’ But I love what I do. And if you truly love what you do then setbacks are just a motivation for you to keep going. You get through it by knowing that it’s vital to have setbacks, or you won’t appreciate it when you make it.”

On Emotions

“I’m not going to make a decision based on emotions or something that may have happened in the past. I have to think about managing them. I make a decision that’s best for the business. And that’s our motto: do what’s best for the business.”

On Burnout

“When I first started, I was close to burnout because I was working from 9:00am until 3:00am. I would be on calls and sending emails because I was acting as the CEO, the COO and the president. I was on a fast track to burnout. You need to have a good team, be able to delegate and have great communication with your team.”

On Taking Risks

“As an athlete, what’s important to me is making the first move. As an entrepreneur, it’s about making the first move and taking a step towards your success. For me, it was making the first move and putting the first money down to invest in the company that I was deciding to build — I probably should have done it years ago.”